Methyl chloroformate → HCID 86706315, compound

Participants

Reaction Steps

6-Bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine (Preparation 22, 100 mg, 0.36 mmol) was dissolved in dry DMF (1 ml). The solution was degassed and a solution of sodium bis(trimethylsilyl)amide (0.55 ml of a 1M solution in THF, 0.55 mmol) was added. After 20 minutes reaction, methylchloroformate (52 mg, 0.55 mmol) was added and the reaction stirred for 2 hours at room temperature. The reaction was diluted with ethyl acetate and water. The organic solution was washed with brine, dried over sodium sulphate and concentrated in vacuum. The crude product was purified on silica gel column chromatography eluting with 20% hexane in ethyl acetate followed by 2% methanol in ethyl acetate to afford the title compound as a white powder (95 mg, 79%). 1H NMR (500 MHz, CDCl3) 3.96 (s, 3H), 4 (s, 3H), 6.57 (s, 1H), 7.63 (s, 1H), 7.64 (s, 1H), 8.1 (s. 1H), 8.53 (s, 1H)

Provenance & Evidence